Pd-Catalyzed Cascade Reactions of Aziridines: One-step Access to Complex Tetracyclic Amines

Knowles, Jonathan, Steeds, Hannah G., Schwarz, Maria, Latter, Francesca and Booker-Milburn, Kevin I. (2021) Pd-Catalyzed Cascade Reactions of Aziridines: One-step Access to Complex Tetracyclic Amines. Organic Letters, 23 (13). pp. 4986-4990. ISSN 1523-7060

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Official URL: https://doi.org/10.1021/acs.orglett.1c01403

Abstract

The combination of palladium catalysis and thermal cycloaddition is shown to transform tricyclic aziridines into complex, stereodefined tetracyclic products in a single step. This highly unusual cascade process involves a diverted Tsuji–Trost sequence leading to a surprisingly facile intramolecular Diels–Alder reaction. The starting materials are accessible on multigram scales from the photochemical rearrangement of simple pyrroles. The tetracyclic amine products can be further elaborated through routine transformations, highlighting their potential as scaffolds for medicinal chemistry.

Item Type: Article
Additional Information: Funding information: The authors thank EPSRC (EP/L05366/1 and EP/S024107/1) and AstraZeneca (H.G.S.) for funding. The authors thank Dr. Hazel Sparkes (University of Bristol) for X-ray crystallography and Paul Lawrence (University of Bristol) for NMR studies.
Uncontrolled Keywords: aziridines, Diels-Alder, domino reactions, palladium, Tsuji-Trost
Subjects: C700 Molecular Biology, Biophysics and Biochemistry
F100 Chemistry
Department: Faculties > Health and Life Sciences > Applied Sciences
Depositing User: Elena Carlaw
Date Deposited: 15 Jun 2021 10:17
Last Modified: 27 Jul 2021 12:00
URI: http://nrl.northumbria.ac.uk/id/eprint/46444

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